13071-11-9

Basic information

• Product Name: (R)-(+)-PROPRANOLOL
• Synonyms: R-PROPANOLOL;R-(+)-PROPANOLOL HCL;(R)-(+)-PROPANOLOL HYDROCHLORIDE;(R)-(+)-PROPRANOLOL;R-PROPRANOLOL;(R)-(+)-PROPRANOLOL HYDROCHLORIDE;(R)-PROPRANOLOL HYDROCHLORIDE;(R)-(+)-1-[(1-METHYLETHYL)AMINO]-3-(1-NAPHTHALENYLOXY)-2-PROPANOL HYDROCHLORIDE
• CAS NO: 13071-11-9
• Molecular Formula: C₁₆H₂₁NO₂*ClH
• Molecular Weight: 295.81
• EINECS: 235-961-7
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 13071-11-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 196-198 °C(lit.)
• Boiling Point: 434.9 °C at 760 mmHg
• Flash Point: 216.8 °C
• Appearance: /
• Vapor Pressure: 2.48E-08mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: ethanol: 10 mg/mL
• BRN: 5780490
• CAS DataBase Reference: (R)-(+)-PROPRANOLOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-PROPRANOLOL(13071-11-9)
• EPA Substance Registry System: (R)-(+)-PROPRANOLOL(13071-11-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 13071-11-9(Hazardous Substances Data)

Usage

Description

(R)-Propranolol hydrochloride is the less active enantiomer of the anti-adrenoceptor (β-adrenoceptor) antagonist propranolol (HY-B0573). Propranolol is a nonselective β-adrenergic receptor (βAR) antagonist with high affinity for β1AR and β2AR with Ki values of 1.8 nM and 0.8 nM, respectively.

Physical Properties

(R)-Propranolol's solubility:ethanol: 10 mg/mLDMSO: <14.5 mg/mLH2O: 50 mg/mL (With heat. Aqueous solutions are most stable at pH 3.0 and decompose rapidly at basic pH. Decomposition is accompanied by discoloration of the solution.)

Uses

Different sources of media describe the Uses of 13071-11-9 differently. You can refer to the following data:
1. less active enantiomer
2. The R-enantiomer of Propranolol (P831800). β?Adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II).

Biochem/physiol Actions

Less active enantiomer of propranolol.

Mechanism of action

Pronolol hydrochloride is a non-selective beta-receptor blocker that blocks beta receptors in the myocardium and has antagonistic effects on beta1 and beta2 receptors. Slow down the heart rate, inhibit cardiac contractility and conduction, reduce circulating blood volume, and reduce myocardial oxygen consumption.

Purification Methods

The hydrochloride is recrystallised from n-PrOH or Me2CO. It is soluble in H2O and EtOH but is insoluble in Et2O, *C6H6 or EtOAc. The racemate has m 163-164o, and the free base recrystallises from cyclohexane with m 96o. [Howe & Shanks Nature 210 1336 1966.] The S-isomer (below) is the physiologically active isomer.

InChI:InChI=1/C16H21NO2.ClH/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16;/h3-9,12,14,17-18H,10-11H2,1-2H3;1H/t14-;/m0./s1

Upstream product

• 318-98-9 Inderal 
• 20133-93-1 1-chloro-3-(1-naphthoxy)-2-propanol 
• 90-15-3 α-naphthol 
• 2461-42-9 3-(1-naphthyloxy)-1,2-epoxypropane 
• 75-31-0 isopropylamine 
• 132005-35-7 (S)-(+)-1-chloro-3-(1-naphthyloxy)-2-propanol 
• 108433-49-4 1-chloro-2-acetoxy-3-(1-naphthyloxy)propane 

Downstream Products

• 91796-22-4 (+)-5-Hydroxypropranolol 
• 393828-92-7 (R)-N-desisopropylpropranolol 
• 227176-55-8 (R)-2-Phenyl-butyric acid (R)-1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester 
• 227176-57-0 (S)-2-Phenyl-butyric acid (R)-1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester 

Relevant articles and documents

Covalent Organic Frameworks with Chirality Enriched by Biomolecules for Efficient Chiral Separation

The separation of racemic compounds is important in many fields, such as pharmacology and biology. Taking advantage of the intrinsically strong chiral environment and specific interactions featured by biomolecules, here we contribute a general strategy is developed to enrich chirality into covalent organic frameworks (COFs) by covalently immobilizing a series of biomolecules (amino acids, peptides, enzymes) into achiral COFs. Inheriting the strong chirality and specific interactions from the immobilized biomolecules, the afforded biomolecules?COFs serve as versatile and highly efficient chiral stationary phases towards various racemates in both normal and reverse phase of high-performance liquid chromatography (HPLC). The different interactions between enzyme secondary structure and racemates were revealed by surface-enhanced Raman scattering studies, accounting for the observed chiral separation capacity of enzymes?COFs.

Ultrafast chiral separations for high throughput enantiopurity analysis

Recent developments in fast chromatographic enantioseparations now make high throughput analysis of enantiopurity on the order of a few seconds achievable. Nevertheless, routine chromatographic determinations of enantiopurity to support stereochemical investigations in pharmaceutical research and development, synthetic chemistry and bioanalysis are still typically performed on the 5-20 min timescale, with many practitioners believing that sub-minute enantioseparations are not representative of the molecules encountered in day to day research. In this study we develop ultrafast chromatographic enantioseparations for a variety of pharmaceutically-related drugs and intermediates, showing that sub-minute resolutions are now possible in the vast majority of cases by both supercritical fluid chromatography (SFC) and reversed phase liquid chromatography (RP-LC). Examples are provided illustrating how such methods can be routinely developed and used for ultrafast high throughput analysis to support enantioselective synthesis investigations.

Combined use of ionic liquid and hydroxypropyl-β-cyclodextrin for the enantioseparation of ten drugs by capillary electrophoresis

In the present study, hydroxypropyl-β-cyclodextrin and an ionic liquid (1-ethyl-3-methylimidazolium-l-lactate) were used as additives in capillary electrophoresis for the enantioseparation of 10 analytes, including ofloxacin, propranolol hydrochloride, dioxopromethazine hydrochloride, isoprenaline hydrochloride, chlorpheniramine maleate, liarozole, tropicamide, amlodipine benzenesulfonate, brompheniramine maleate, and homatropine methylbromide. The effects of ionic liquid concentrations, salt effect, cations, and anions of ionic liquids on enantioseparation were investigated and the results proved that there was a synergistic effect between hydroxypropyl-β-cyclodextrin and the ionic liquid, and the cationic part of the ionic liquid played an important role in the increased resolution. With the developed dual system, all the enantiomers of 10 analytes were well separated in resolutions of 5.35, 1.76, 1.85, 2.48, 2.88, 1.43, 5.45, 4.35, 2.76, and 2.98, respectively. In addition, the proposed method was applied to the determination of the enantiomeric purity of S-ofloxacin after validation of the method in terms of selectivity, repeatability, linearity range, accuracy, precision, limit of detection (LOD), and limit of quality (LOQ). Chirality 25:409-414, 2013.